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Compare 582 Vacation Homes in Chester with updated reviews, rates, and availability.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (205)
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (37)
Calloway Drive Retreat | House in Shady Side
Calloway Drive Retreat | House in Shady Side
9.2 out of 10, Wonderful, (5)
Dollhouse in Central Historic St Michaels
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (46)
Private Waterfront Woods | Dock, Kayaks, Views
Private Waterfront Woods | Dock, Kayaks, Views
9.8 out of 10, Exceptional, (15)
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (108)
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (72)
Waterfront family resort Lodge with private pier, game room and bar
Waterfront family resort Lodge with private pier, game room and bar
9.8 out of 10, Exceptional, (23)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (8)
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (205)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (23)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Chester hotels
Recent reviews of Chester hotels
5/5 Excellent
"Absolutely beautiful Inn "
A verified traveler stayed at Historic Inns of Annapolis
Posted 13 hours ago